Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates

The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 °C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The hi...

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Bibliographic Details
Published inTetrahedron Vol. 74; no. 44; pp. 6426 - 6441
Main Authors Weischedel, Heike, Schmidt, Dietmar, Conrad, Jürgen, Beifuss, Uwe
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.11.2018
Elsevier
Subjects
1,2-Addition
Chemistry
Chemistry, Organic
Copper
Cross-coupling
Domino reaction
N-Vinylation
Physical Sciences
Science & Technology
Cross-coupling
N-Vinylation
Copper
1,2-Addition
Domino reaction
BENZIMIDAZOLE DERIVATIVES
ONE-STEP SYNTHESIS
BUILDING-BLOCKS
DOMINO ADDITION/DOUBLE CYCLIZATION
COPPER-CATALYZED SYNTHESIS
PROPARGYLIC ALCOHOLS
REACTIONS EFFICIENT
SELECTIVE SYNTHESIS
PEPTIDE-SYNTHESIS
O-HALOANILINES
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Summary:The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 °C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The highly selective transformation is assumed to start with an intermolecular 1,2-addition, which is followed by an intramolecular N-vinylation. The products can also be obtained in the absence of Cu2O, albeit in lower yields. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2018.08.051